It's Now or Never!
by cultofwinters
Summary: Gary Oak has had kept his silence long enough. He wants to go to the Kalos region to confess his true feelings. Does Ash feel the same way? Read on to learn more!


**Heyoooo! I'm back from the dead! First of all, thank you all soooo much for being so patient with me! I feel dreadful that I haven't given y'all an update or new stuff in like, two months! Holy cow! But, I'm "back?" Hope you enjoy this two-chapter story thing! Please review, and, bye!**

 **Disclaimer: I do NOT own Pokemon, or ANY of the registered/trademarked Characters! I just own the plot!**

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Gary Oak rolled his eyes and let out an exasperated sigh as he stared longingly out his window. It was on days like these that he wanted one person next to him, Ash Ketchum. They hadn't talked since Ash came back from the Unova region around three years prior. Gary regretted being too busy in his paperwork to at least speak to him.

He also knew that Misty still had a bit of a crush on Ash, but she didn't know about his feelings for the young man. Of course, she was quite attractive herself and was no longer a scrawny ten-year-old girl.

Gary shook his head of those thoughts and refocused them on the Raven-haired boy he had grown to yearn for. He sighed again and glanced to the outside world once more.

It was such a lovely day, and he was spending it doing research. The brunette tossed his pencil to the side and got up

"Ah, there you are Gary! Finally taking a break, I see!" Prof. Oak beamed at the sight of his grandson, "Yep, I need to stretch out a little, I'm going over to Mrs. Ketchum's house if that's ok?" Gary asked, "Of course! Oh, and could you do me a huge favor?" The Prof. walked over to the young researcher, who nodded in response. "Eat!" Prof. Oak shouted. "Yes, Grandpa! I will! See ya later!" And with that the young aspiring, Kanto researcher took off.

There was a gentle breeze flowing through Gary's wild spiky brown hair, and he relished it for a few moments as he walked down the road to the Ketchum abode. He rung the doorbell and waited for an answer

"Why, hello there Gary! It's been quite a while!" Delia Ketchum beamed as she opened the door, "Hey, there Mrs. K! Sorry I haven't come by" Gary apologized while rubbing the back of his head

"Well, don't just stand there, get in here, and give me a hug!" Delia let him in, "You know you don't have to knock or ring the doorbell Gary, you're always welcome here" the older woman smiled as the young man chuckled and hugged her

"I know Mrs. K! But you know I don't listen!" He snickered, Delia grinned and rolled her eyes then lightly jabbed him in the stomach, "Arceus, Gary! You look so thin!" she scolded in a motherly tone, "Have you been eating? And answer me truthfully young man." She crossed her arms and frowned at him. "Y-yes Ma'am! Although I haven't really been hungry all that much, I just..." Gary trailed off. "This is about Ash, isn't it?" Delia cooed. There was no point in arguing with her; she was practically his mother

"Yes Ma'am," he said sullenly, "I can't stop thinking about him" the aspiring Pokemon Professor looked up at Ash's mom, surprised to see a smile on her face. "Gary Oak, I've known that you have loved my son since you were a young boy. He's the closest thing you have to a brother, and I know you were hurt so badly when your parents passed" Delia wrapped her arms around him.

"Thank you, Mrs. Ketchum," Gary grinned, and a loud growling sound from his stomach made him blush. "Oh, dear! Sounds like someone's hungry!" Delia giggled, "Help yourself, but if I don't see you going for seconds, I will scold you Gary Oak!" Delia smirked at the young man. "Yes, Ma'am!"

After Gary had three servings, he washed his plate and sat on the couch, rubbing his stomach. "Oh, my Arceus, Mrs. K! That was the best meal I've had in months!" Gary exclaimed. "I'm glad you liked it!" Delia replied, and sat down on another couch in the living room.

"So, are you going to go see him?" the older woman asked, Gary smiled and nodded, slowly dozing off. "I'm sorry, Mrs. Ketchum!" The young man woke with a start. "You're fine, dear, go ahead and rest, if you want, we'll talk later" Delia smiled.

She was about to ask him something else, but the sound of him snoring put her mind at ease. She put a blanket on him and kissed his forehead. "Thank you...Mom" He whispered and fell back to sleep.

Of course, Delia wasn't his birth or adopted mother. Gary used that name for her because she was the only motherly figure in his life. He didn't use that nickname very often, so it was very special to her. She went up the stairs and went to bed.

The next morning, Delia Ketchum woke up to what smelled like burnt toast. She shook her head, got out of bed and walked downstairs. The older woman giggled quietly to herself as she heard Gary whispering curses at himself for being an incompetent little.

"Good Morning Gary!" Delia gingerly sauntered into the kitchen. Gary yelped in surprise and nearly dropped a set of plates. "Oh, Arceus! Wow!" The young researcher smiled and grabbed his chest. "Having a little trouble here?" Delia giggled and raised an eyebrow. Gary laughed nervously and rubbed the back of his neck.

"Mr. Mime!" The Mime Pokemon walked into the kitchen, "Good Morning Mimey!" Delia chirped, and the Pokemon hugged her. The doorbell rang, and the loyal mime Pokemon dutifully answered the door. "Why hello there, Mr. Mime!" Prof. Oak cheerfully exclaimed. "Come on in, Prof. Oak! Gary is in the kitchen as well!" Delia called and started making breakfast for the company. "Oh, Delia! I already ate!" Prof. Oak chuckled and greeted his grandson, "Well, you can eat again!" Delia giggled and got back to her task.

Much like his grandson, Samuel Oak knew not to argue with her, so he poured himself some coffee and sat down. "Gramps, Mrs. K, I have decided I want to go see Ash", Gary informed them confidently. "That's wonderful Gary! I'm sure he'd love to see you!" Prof. Oak beamed. "Oh, and make sure you take some Pokemon with you, I've heard he has grown to be a formidable trainer!" Oak added as Delia served them a plate of eggs, bacon, pancakes, hash browns, and sausage. "Oh, goodness! Did I give you too much Samuel?" Delia asked in a worried tone, "I actually haven't eaten yet, so that'll fill me up till dinner!" Prof. Oak guffawed and dug in.

"My goodness, Gary! Did you want to leave now?" Delia raised her eyebrow as the young researcher scarfed down two plates full of pancakes. Gary finished chewing before he answered. "I found a flight leaving to the Kalos region in five hours! I've got to go pack! Goodbye Mrs. K! Thank you for everything!" Gary almost bolted out of the door; he slid back into the kitchen and kissed Delia's head, "Bye Gramps! I'll see you in a few days!" Gary closed the door behind him.

The brunette young researcher bounded upstairs to his room, his Umbreon was not too thrilled that her trainer was making so much noise this early in the morning. She growled to voice her frustration, "Oh! Sorry Umbreon! I am going to the Kalos region to go see Ash, and hopefully" Gary turned to his nightstand where his half of a Poke ball sat, and he grinned ear to ear, "Hopefully we'll be more than best friends when I tell him the truth!" Gary held the item to his chest and sighed with content. The dark type eeveelution was still upset from being woken up, but rubbed her body against her trainer's leg and mewled happily.

After packing his clothes and toiletries: Gary got a small team of his best Pokemon, he could try giving Ash a challenge; but he'd probably loose anyway. He shut off all the lights in his house, threw everything in the trunk, and sped off to the airport.

Getting through all the lines was pure hell; dealing with impatient people was slowly aggravating the young man. "Come on, Gary! Don't loose your cool!" He scolded himself quietly.

Once the brunette researcher made it to his gate, he sat down, pulled out his laptop, and tried to relax.

"Excuse me, Mr. Oak? Mr. Oak?" Gary's eyes shot open, and he almost hit the woman that woke him. "Did I miss my flight? How long was I asleep? Was I snoring too loud?" Gary asked in one breath. "Everything is alright, Mr. Oak. The pilot has upgraded you to first class!" she cheered. Gary sighed in relief, gathered his belongings, and thanked the woman.

The young researcher grinned ear to ear as the plane touched down after fifteen hours of travel time. Gary didn't waste any time gathering his suitcase and making his way to the bus that would take him to the hotel in Lumiose City. He couldn't help but marvel at the various new sights and Pokemon he had never even heard of.

"I need to find out where Ash is," Gary told himself once he got off the bus. He stopped by the nearby Pokemon Center and called Ash's mom. "Hello?" she answered, "Hey, Mrs. K! I made it safely to the Kalos region!" He grinned. "Excellent! I got off the phone with Ash an hour ago, and he and his friends are in Lumiose City right now! And don't worry, I didn't tell him you were going!" Delia smirked. "Ok, thank you Mrs. K! Wish me luck!" Gary crossed his fingers. "I will have a big supper for you both when you come back, bye, Gary!"

And with that, Gary kissed a photo of his soon to be future boyfriend, "I'm coming Ash!"

Back in Pallet Town: Tracey Sketchit pulled into Prof. Oak's laboratory early in the morning. "Good Morning Professor!" the young man gingerly greeted, "Ah! Good morning to you too, Tracey!" Prof. Oak beamed.

Looking around the room, Tracey would usually see Gary at his desk, "Prof. Oak, is Gary not coming in today?" He asked, "No, he went to the Kalos region to go see Ash, it's about time he got out too!" the Prof. laughed heartily.

"Good for him!" Tracey cheered. He knew about Gary's feelings for Ash and was glad that he finally got the courage to go tell him. The Pokemon watcher felt his phone vibrating; it was a text from Ash.

"Wow, I didn't know Ash had a...phone" Tracey opened the message, "Oh, no! Gary doesn't know he's with.

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 **End of Ch. 1**

 **A/N:**

 **Cliffhanger! LOL! Please put your guesses in the review section! Is it Serena, Misty or someone else?! Sorry, I have been gone for SO long! But, I have a couple of stories that are ALREADY finished, and I will try to post them in the ensuing weeks. I will be uploading the Advanceshipping one-shot in June! Thanks for voting! Please review, and I'll catch y'all lovely people later!**

 **Until Next Time!**

 **Written and edited by Cultofwinters**


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